4748-78-1

Basic information

• Product Name: 4-ethylbenzaldehyde
• Synonyms: 1,5-dioxaspiro[5.5]undecan-3-ol, 8-methyl-; 8-Methyl-1,5-dioxaspiro[5.5]undecan-3-ol
• CAS NO: 4748-78-1
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.1751
• EINECS: 225-268-8
• Product Categories: Thiophenes ,Thiazolines/Thiazolidines;Aromatic Aldehydes & Derivatives (substituted);Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Benzaldehyde;Benzaldehyde (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Alphabetical Listings;E-F;Flavors and Fragrances;Aldehydes;C9;Carbonyl Compounds
• Mol File: 4748-78-1.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 221.7°C at 760 mmHg
• Flash Point: 92.2°C
• Density: 1.001g/cm³
• Vapor Pressure: 0.106mmHg at 25°C
• Refractive Index: 1.548
• Water Solubility: Not miscible or difficult to mix in water. Soluble in alcohol.
• BRN: 636027
• CAS DataBase Reference: 4-ethylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ethylbenzaldehyde(4748-78-1)
• EPA Substance Registry System: 4-ethylbenzaldehyde(4748-78-1)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:; R36/37/38:
• Safety Statements: S26:; S37/39:
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 4748-78-1(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 4748-78-1 differently. You can refer to the following data:
1. CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
2. 4-Ethylbenzaldehyde has a sweet, bitter-almond odor

Occurrence

Reported found in roasted turkey, grilled and roasted beef, roasted chicken, cider, black tea, roasted peanuts and cooked trassi

Uses

Different sources of media describe the Uses of 4748-78-1 differently. You can refer to the following data:
1. It is used as a perfuming agent in cosmetics industry. It is also used as a pharmaceutical intermediate.
2. 4-Ethylbenzaldehyde has been used in the synthesis of 4,4′-diaminotriphenylmethanes under microwave irradiation, which is useful for parallel library syntheses.

Aroma threshold values

Detection: 13 ppb; recognition: 40 ppb

Synthesis Reference(s)

Synthetic Communications, 26, p. 315, 1996 DOI: 10.1080/00397919608003620

General Description

4-Ethylbenzaldehyde is a by-product of disinfection. Kinetic constants (KI) of 4-ethylbenzaldehyde for inhibition of the diphenolase activity of mushroom tyrosinase has been investigated.

Synthetic route

4-Ethynylbenzaldehyde (63697-96-1) → 4-vinyl-benzaldehyde (1791-26-0) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With hydrogen In tetrahydrofuran at 50℃; under 760.051 Torr; for 10h;	A 97% B 3%
With hydrogen In dichloromethane at 40℃; under 1500.15 Torr; for 24h; Reagent/catalyst; Solvent; Temperature; Pressure; Schlenk technique;	A 67 %Chromat. B 33 %Chromat.

4-ethylbenzyl alcohol (768-59-2) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With iron(III) chloride; nitric acid In acetone at 20℃; for 0.233333h; Sonication;	95%
With 3,3-dichloro-1,2-diphenylcyclopropene; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;	95%
With laccase; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In tetrahydrofuran; water at 40℃; for 24h;	92%

4-ethylbenzylamine (7441-43-2) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With immobilised amine transaminase from the moderate halophilic bacterium Halomonas elongata; sodium pyruvate In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 760.051 Torr; for 2h; pH=8;	94%
With steam; nickel at 210℃;

1-bromo-4-ethylbenzene (1585-07-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With samarium; copper(l) iodide at 20℃; for 4h; Inert atmosphere;	93%

1-ethenyl-4-ethyl-benzene (3454-07-7) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 65℃; for 6h;	92%

4-vinyl-benzaldehyde (1791-26-0) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With methanol; formic acid; water In ethyl acetate at 25℃; for 3h; Irradiation; Inert atmosphere;	90%
With aluminum (III) chloride In ethanol; water; acetonitrile at 20℃; for 6h; Irradiation; Inert atmosphere;	95 %Chromat.

C13H16O4 → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 20℃; for 2.5h; chemoselective reaction;	86%

p-ethylbenzoic acid (619-64-7) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With succinic acid anhydride; methylphenylsilane; C58H82O6P2; copper(II) nitrate In tetrahydrofuran at 75℃; for 18h; Schlenk technique; Inert atmosphere;	85%
With potassium phosphate; sodium hypophosphite; 2,2-dimethylpropanoic anhydride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 16h;	74%
With 2,6-dimethylpyridine; nickel(II) bromide trihydrate; phenylsilane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate at 60℃; for 24h; Schlenk technique; Inert atmosphere;	76 %Chromat.

formic acid (64-18-6) + 4-ethyl-1-iodobenzene (25309-64-2) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
Stage #1: formic acid; 4-ethyl-1-iodobenzene With palladium diacetate; acetic anhydride; tricyclohexylphosphine In N,N-dimethyl-formamide at 30℃; for 1h; Inert atmosphere; Green chemistry; Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Green chemistry;	85%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	71%

α,α-dibromo-p-toluene + dimethyl sulfoxide (67-68-5) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
at 100℃; for 5h;	80%

carbon dioxide (124-38-9) + ethylbenzene (100-41-4) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
Stage #1: carbon dioxide With zinc(II) cyanide; ruthenium trichloride; rhodium (III) acetate; cobalt(II) acetate; zirconium(IV) acetate for 1h; Autoclave; Stage #2: ethylbenzene at 50℃; under 15001.5 Torr; for 5h;	80%

triethyl borane (97-94-9) + 4-(trifluormethanesulfonyloxy)benzaldehyde (17763-69-8) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Reflux; Inert atmosphere;	78%

sodium 4-ethylbenzylate → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With 4-ethylbenzyl alcohol; 1,2-dimethylindazolium chloride for 3h; Heating;	71%

4-methylethylbenzene (622-96-8) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With tert.-butylhydroperoxide at 120℃; for 5h; Sealed tube; Green chemistry;	70%

p,p'-diethyldiphenylmercury (10217-72-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With trichlorophosphate In water at 70℃; for 5h;	65%

ethyllithium (811-49-4) + 4-bromo-N-methoxy-N-methylbenzamide (192436-83-2) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
Stage #1: 4-bromo-N-methoxy-N-methylbenzamide With diisobutylaluminium hydride In hexane; toluene at 0 - 20℃; Inert atmosphere; Schlenk technique; Stage #2: ethyllithium In hexane; toluene at 20℃; Inert atmosphere; Schlenk technique;	61%

ethene (74-85-1) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube; Irradiation;	54%

ethene (74-85-1) + 4-bromo-benzaldehyde (1122-91-4) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); N,N,N,N,-tetramethylethylenediamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; water; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube; Irradiation;	50%

4-ethyl-1-cyclopropylbenzene (35076-76-7) → (E)-3-(4-ethylphenyl)acrylaldehyde (127506-37-0) + 5-(4-ethylphenyl)isoxazoline (119200-33-8) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With dinitrogen tetraoxide; triethylamine In dichloromethane at -30℃; for 1h;	A 32% B 48% C 8%
With dinitrogen tetraoxide In dichloromethane at -30℃; for 1h;	A 35% B 40% C 8%

1-cyclopropyl-4-methyl-benzene (6921-43-3) → (E)-3-(4-ethylphenyl)acrylaldehyde (127506-37-0) + 5-(4-ethylphenyl)isoxazoline (119200-33-8) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With dinitrogen tetraoxide In dichloromethane at -30℃; for 1h;	A 35% B 40% C 8%

(4-ethyl-benzyliden)-aniline (67302-72-1) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With sulfuric acid
With sulfuric acid

N-(4-ethyl-benzylidene)-p-toluidine (246161-07-9) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With sulfuric acid

4-ethylbenzylchloride (1467-05-6) → 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With hexamethylenetetramine

4-methylethylbenzene (622-96-8) → para-methylacetophenone (122-00-9) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With oxygen; iron(II) chloride; zinc; iron(III) In pyridine; acetic acid for 16h;	A 10.3 % Chromat. B 3.1 % Chromat.
With oxygen; acetic acid; iron(II) chloride; zinc; iron(III) In pyridine for 16h; Product distribution; other alkylbenzenes; without Fe(III)-catalyst;
With oxygen In acetonitrile at 24.84℃; under 760.051 Torr; Reagent/catalyst; Irradiation; Green chemistry;

4-methylethylbenzene (622-96-8) → 1-ethenyl-4-methylbenzene (622-97-9) + CH3C6H4CH(CH3)OH (536-50-5) + para-methylacetophenone (122-00-9) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With ammonium peroxydisulfate; copper diacetate In water; acetonitrile at 100℃; Yield given. Further byproducts given. Yields of byproduct given;
With ammonium peroxydisulfate; copper diacetate; sodium acetate In water; acetonitrile at 100℃; Yield given. Further byproducts given. Yields of byproduct given;

4-methylethylbenzene (622-96-8) → 1-ethenyl-4-methylbenzene (622-97-9) + 4-ethylbenzyl acetate (67035-84-1) + para-methylacetophenone (122-00-9) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With ammonium peroxydisulfate; copper diacetate In water; acetic acid at 100℃; Yield given. Further byproducts given. Yields of byproduct given;

N-tert-butyl α-(4-ethylphenyl) nitrone (85623-71-8, 137957-42-7) → N-tert-Butylhydroxylamine (16649-50-6) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With water at 25℃; Rate constant; hydrolysis;

C13H19NO → N-n-butylhydroxylamine (5080-24-0) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With water; hydrogen cation In various solvent(s) at 25℃; Rate constant; Mechanism; pH=1.00; rate constant - octanol/water partition coefficient and relative rate - substituent constants correlations in lamellar solvent;

4-methylethylbenzene (622-96-8) → 1-ethenyl-4-methylbenzene (622-97-9) + 4-ethylbenzyl alcohol (768-59-2) + para-methylacetophenone (122-00-9) + 4-ethylbenzylaldehyde (4748-78-1)

Conditions	Yield
With nitrate radical under 760 Torr; Kinetics; Oxidation;

4-Butylaniline (104-13-2) + 4-ethylbenzylaldehyde (4748-78-1) → 4-butyl-N-[(1E)-(4-ethylphenyl)methylene]aniline (1046769-82-7)

Conditions	Yield
In ethanol Reflux; Inert atmosphere;	100%

propylamine (107-10-8) + 4-ethylbenzylaldehyde (4748-78-1) → N-(4-ethylbenzylidene)propan-1-amine (1246401-39-7)

Conditions	Yield
at 20℃; for 12h;	100%
at 20℃; for 1h;

4-ethylbenzylaldehyde (4748-78-1) + methylamine (74-89-5) → N-(4-ethylbenzylidene)methanamine (1246401-40-0)

Conditions	Yield
at 20℃; for 12h;	100%
at 20℃; for 1h;
In dichloromethane at 20℃; for 4h;

ketene t-butyldimethylsilyl methyl acetal (77086-38-5) + 4-ethylbenzylaldehyde (4748-78-1) → C18H30O3Si (1231743-50-2)

Conditions	Yield
With silver hexafluoroantimonate; 2,6-bis-[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) chloride In dichloromethane at 20℃; Mukaiyama Aldol Addition; Inert atmosphere;	100%
With C33H29FeNO2P(1+)*I(1-) In acetonitrile at 20℃; for 0.25h; Mukaiyama aldol reaction;	48%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-ethylbenzylaldehyde (4748-78-1) → C26H34N2 (1217526-83-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

4-ethylbenzylaldehyde (4748-78-1) + 3-hydrazinylpropanenitrile (353-07-1) → C12H15N3

Conditions	Yield
at 20℃;	100%

4-ethylbenzylaldehyde (4748-78-1) + 1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → 1-(2,4-dichlorophenyl)-3-(4-ethylphenyl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 15h; Claisen-Schmidt Condensation;	100%

4-ethylbenzylaldehyde (4748-78-1) → 4-ethylbenzyl alcohol (768-59-2)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 0.25h;	99%
With formaldehyd; C42H36ClIrO2P2; triethylamine In 1,2-dimethoxyethane at 80℃; for 20h; Reagent/catalyst; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%
With sodium tetrahydroborate In methanol for 14h;	98%

2-thioxo-4-thiazolidinone (141-84-4) + 4-ethylbenzylaldehyde (4748-78-1) → (5Z)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

Conditions	Yield
With ammonium acetate; acetic acid for 1h; Reflux; stereoselective reaction;	99%
With ammonium acetate; acetic acid for 1 - 12h; Heating / reflux;

triethylsilane (617-86-7) + 4-ethylbenzylaldehyde (4748-78-1) → triethyl((4-ethylbenzyl)oxy)silane (1163144-08-8)

Conditions	Yield
With C42H43BN3P2(1+)*C18HBF15(1-) In chloroform at 40℃; for 1h; Reagent/catalyst; Temperature; Schlenk technique; Glovebox;	99%

para-chloroacetophenone (99-91-2) + 4-ethylbenzylaldehyde (4748-78-1) → (2E)-1-(4-chlorophenyl)-3-(4-ethylphenyl)prop-2-en-1-one (343610-66-2)

Conditions	Yield
Stage #1: para-chloroacetophenone; 4-ethylbenzylaldehyde With sodium methylate In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In methanol; water	98%
With potassium hydroxide In ethanol at 20℃; Claisen-Schmidt Condensation;

para-chloroacetophenone (99-91-2) + 4-ethylbenzylaldehyde (4748-78-1) → 1-(4-chloro-phenyl)-3-(4-ethyl-phenyl)-propenone (782483-60-7)

Conditions	Yield
Stage #1: para-chloroacetophenone; 4-ethylbenzylaldehyde With sodium methylate In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In methanol; water	98%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + 4-ethylbenzylaldehyde (4748-78-1) → (2R,5S)-2-(4-ethylphenyl)-3-methyl-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)oxazolidine (1042065-80-4)

Conditions	Yield
In benzene Heating;	98%

phenylhydrazine (100-63-0) + 4-ethylbenzylaldehyde (4748-78-1) → 1-(4-ethylbenzylidene)-2-phenylhydrazine (324067-43-8)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane	98%
In dichloromethane at 20℃; for 0.5h;
In ethanol; water at 80℃;

2-oxo-propionic acid (127-17-3) + 4-ethylbenzylaldehyde (4748-78-1) → (R)-1-(4-ethylphenyl)-1-hydroxypropan-2-one

Conditions	Yield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;	98%

2-acetyl-5-chlorothiophene (6310-09-4) + 4-ethylbenzylaldehyde (4748-78-1) → (2E)-1-(4-chlorocyclopenta-1,3-dien-1-yl)-3-(4-ethylphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 4h;	98%

4-hydroxy-6-methyl-2-pyridone (3749-51-7) + 4-ethylbenzylaldehyde (4748-78-1) + malononitrile (109-77-3) → 2-amino-7-methyl-5-oxo-4-(4-ethylphenyl)-5,6-dihydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile

Conditions	Yield
With sodium acetate In ethanol for 1h; Reflux;	98%

N-Phenylglycine (103-01-5) + 4-ethylbenzylaldehyde (4748-78-1) → 1-(4-ethylphenyl)-2-(phenylamino)ethan-1-ol

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In water at 20℃; for 3h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;	98%

4-hydroxy-2(5H)-furanone (541-57-1) + dimedone (126-81-8) + 4-ethylbenzylaldehyde (4748-78-1) → C21H22O4

Conditions	Yield
With yttria doped hydroxyapatites In ethanol at 20℃; Reagent/catalyst; Temperature; Green chemistry;	98%

phthalic anhydride (85-44-9) + ethyl 2-cyanoacetate (105-56-6) + 4-ethylbenzylaldehyde (4748-78-1) → ethyl 3‑amino‑1‑(4‑ethylphenyl)‑5,10‑dioxo‑5,10‑dihydro‑1H‑pyrazolo[1,2‑b]phthalazine‑2‑carboxylate

Conditions	Yield
With hydrazine hydrate In water at 60℃; for 0.75h; Green chemistry;	98%

p-toluene sulfinic acid (536-57-2) + urea (57-13-6) + 4-ethylbenzylaldehyde (4748-78-1) → N-[(4-ethylphenyl)(tosyl)methyl]urea

Conditions	Yield
Stage #1: p-toluene sulfinic acid; 4-ethylbenzylaldehyde In water at 20℃; for 0.416667h; Stage #2: urea In water at 20℃; for 20h;	98%

4-ethylbenzylaldehyde (4748-78-1) + 1,4-phenylenediamine (106-50-3) → bis(4-ethylbenzylidene)-p-phenylenediamine (28784-88-5)

Conditions	Yield
In ethanol for 3h;	97%
In methanol

4-Butylaniline (104-13-2) + 4-ethylbenzylaldehyde (4748-78-1) → N-(4-n-ethylbenzylidene)-4'-n-butylaniline (54379-33-8)

Conditions	Yield
	97%

4-ethylbenzylaldehyde (4748-78-1) → sodium (4-ethylphenyl)(hydroxy)methanesulfonate (1174516-81-4)

Conditions	Yield
With sodium hydrogensulfite In ethanol; water for 20.5h; Inert atmosphere;	97%
With sodium metabisulfite; water In ethanol Cooling;

benzoic acid hydrazide (613-94-5) + allyl bromide (106-95-6) + 4-ethylbenzylaldehyde (4748-78-1) → N'-[1-(4-ethylphenyl)but-3-en-1-yl]benzohydrazide (1449037-68-6)

Conditions	Yield
With zinc perchlorate; indium In methanol at 20℃; for 4h; chemoselective reaction;	97%

[(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) + 4-ethylbenzylaldehyde (4748-78-1) → 5-(4-ethylphenyl)oxazole

Conditions	Yield
With potassium carbonate at 80℃; for 1.5h;	97%

4-ethylbenzylaldehyde (4748-78-1) + malononitrile (109-77-3) → 2-[(4-ethylphenyl)methylidene]propanedinitrile

Conditions	Yield
With biguanide-functionalized hierarchical porous covalent organic framework In water at 20℃; for 0.166667h; Knoevenagel Condensation;	97%
With dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate In water at 40℃; for 2h; Knoevenagel Condensation;	95%
Stage #1: 4-ethylbenzylaldehyde With C9H11ClN2O*ClHO4 In neat (no solvent) for 0.166667h; Knoevenagel Condensation; Stage #2: malononitrile In neat (no solvent) at 25 - 30℃; for 0.5h; Knoevenagel Condensation;	94%

Methyl diethylphosphonoacetate (1067-74-9) + 4-ethylbenzylaldehyde (4748-78-1) → 3-(4-ethylphenyl)acrylic acid methyl ester (87087-37-4)

Conditions	Yield
Stage #1: Methyl diethylphosphonoacetate With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-ethylbenzylaldehyde In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	97%

2-amino-benzthiazole (136-95-8) + ethyl 2-cyanoacetate (105-56-6) + 4-ethylbenzylaldehyde (4748-78-1) → C21H21N3O2S

Conditions	Yield
With 2.5 wt% vanadium oxide loaded on fluorapatite In ethanol at 20℃; for 0.5h; Green chemistry;	97%

Upstream product

• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 74-90-8 hydrogen cyanide 
• 100-41-4 ethylbenzene 
• 108-90-7 chlorobenzene 
• 622-96-8 4-methylethylbenzene 
• 7664-93-9 sulfuric acid 
• 619-64-7 p-ethylbenzoic acid 
• 97-94-9 triethyl borane 
• 17763-69-8 4-(trifluormethanesulfonyloxy)benzaldehyde 
• 63697-96-1 4-Ethynylbenzaldehyde 
• 124-38-9 carbon dioxide 
• 67302-72-1 (4-ethyl-benzyliden)-aniline 
• 246161-07-9 N-(4-ethyl-benzylidene)-p-toluidine 

Downstream Products

• 94109-49-6 3-(4-ethyl-phenyl)-2,3-epoxy-propionic acid ethyl ester 
• 64518-49-6 4-(((4-ethylphenyl)methyl)amino)benzoic acid 
• 7561-67-3 2-<4-Ethyl-phenyl>-indan-1,3-dion 
• 81734-57-8 4,4'-diethyl-cis-stilbene 
• 70264-58-3 4,4'-diethyl-trans-stilbene 
• 768-59-2 4-ethylbenzyl alcohol 
• 619-64-7 p-ethylbenzoic acid 
• 100-46-9 benzylamine 
• 302596-35-6 [1-(4-Ethyl-phenyl)-meth-(E)-ylidene]-quinolin-6-yl-amine 

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The enzyme/cofactor system laccase/2,2'-azino-bis(3 ethyl-benzothiazoline-6-sulfonic acid) catalyzes the oxidation of benzyl alcohols to the corresponding benzaldehydes by molecular oxygen. The reaction proceeds under physiological conditions to yield the products quantitatively.

Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes

Nickel-catalyzed reduction of (het)arenecarboxylic acids with hydrosilanes in the presence of dimethyl dicarbonate as the activator affords the corresponding aldehydes. The role of the activator is the conversion of the acids into their anhydrides undergoing C–O cleavage. The good yields were achieved in case of substrates bearing electron-donating and electron-neutral groups.

Photoredox-Catalyzed Simultaneous Olefin Hydrogenation and Alcohol Oxidation over Crystalline Porous Polymeric Carbon Nitride

Booming of photocatalytic water splitting technology (PWST) opens a new avenue for the sustainable synthesis of high-value-added hydrogenated and oxidized fine chemicals, in which the design of efficient semiconductors for the in-situ and synergistic utilization of photogenerated redox centers are key roles. Herein, a porous polymeric carbon nitride (PPCN) with a crystalline backbone was constructed for visible light-induced photocatalytic hydrogen generation by photoexcited electrons, followed by in-situ utilization for olefin hydrogenation. Simultaneously, various alcohols were selectively transformed to valuable aldehydes or ketones by photoexcited holes. The porosity of PPCN provided it with a large surface area and a short transfer path for photogenerated carriers from the bulk to the surface, and the crystalline structure facilitated photogenerated charge transfer and separation, thus enhancing the overall photocatalytic performance. High reactivity and selectivity, good functionality tolerance, and broad reaction scope were achieved by this concerted photocatalysis system. The results contribute to the development of highly efficient semiconductor photocatalysts and synergistic redox reaction systems based on PWST for high-value-added fine chemical production.

Hydroxylamine promoted Fe(III)/Fe(II) cycle on ilmenite surface to enhance persulfate catalytic activation and aqueous pharmaceutical ibuprofen degradation

This study demonstrates a new system for the degradation of emerging pharmaceutical contaminants (e.g., ibuprofen) in water by coupling the naturally occurring ilmenite with hydroxylamine (HA) and persulfate (PS). Ilmenite was able to activate persulfate to generate sulfate radicals (SO4?·) and hydroxyl radicals (HO·). The radical generation was greatly improved by adding small amount of hydroxylamine into the solution, due to the efficient Fe(III)/Fe(II) cycle on the ilmenite surface promoted by HA, which was confirmed by X-ray photoelectron spectroscopy and electron paramagnetic resonance (EPR) spectroscopy analysis. SO4?· and HO· contributed comparably to ibuprofen degradation, which was verified by the radical scavenging tests. The degradation was enhanced with increasing ilmenite, PS and HA dosages, but the HA exhibited strong scavenging effect at its high concentrations. The ilmenite/PS/HA process worked well in the real treated wastewater, because the surface-controlled radical generation was less affected by the water matrix. However, the formation of bromate in the bromide-containing water by this process should be concerned. Ibuprofen was partially mineralized, and the degradation products were identified by ESI-tqMS. A radical-induced degradation pathway was proposed based on the product identification. This work provides the mechanistic insights on persulfate activation based on the surface-controlled catalytic processes. It also offers a new strategy to degrade emerging contaminants in water and sheds light on the environmental functions of natural minerals.